59142-71-1

Upstream product

• 591-51-5 phenyllithium 
• 74-88-4 methyl iodide 
• 6630-33-7 ortho-bromobenzaldehyde 
• 59142-47-1 (2-bromophenyl)phenylmethanol 
• 67-56-1 methanol 

Downstream Products

• 59142-29-9 1'-methyl-3-phenyl-3H-spiro[isobenzofuran-1,4'-piperidine] 
• 59142-31-3 1'-benzyl-3-phenyl-3H-spiro[isobenzofuran-1,4'-piperidine] 
• 84655-51-6 4-hydroxy-4-<2-(1-methoxy-1-phenylmethyl)phen-1-yl>-2,3,5,6-tetrahydropyran 
• 59143-18-9 1'-ethyl-3-phenyl-3H-spiro[isobenzofuran-1,4'-piperidine] 
• 59143-42-9 1'-isopropyl-3-phenyl-3H-spiro[isobenzofuran-1,4'-piperidine] 
• 59143-09-8 1'-acetyl-3-phenyl-3H-spiro[isobenzofuran-1,4'-piperidine] 
• 59143-19-0 3-phenyl-1'-propyl-3H-spiro[isobenzofuran-1,4'-piperidine] 
• 59143-39-4 1'-(3-methyl-but-2-enyl)-3-phenyl-3H-spiro[isobenzofuran-1,4'-piperidine] 
• 60081-39-2 1'-isobutyl-3-phenyl-3H-spiro[isobenzofuran-1,4'-piperidine] 
• 59143-20-3 1'-butyl-3-phenyl-3H-spiro[isobenzofuran-1,4'-piperidine] 
• 59143-10-1 3-phenyl-1'-propionyl-3H-spiro[isobenzofuran-1,4'-piperidine] 
• 60081-65-4 1'-isobutyryl-3-phenyl-3H-spiro[isobenzofuran-1,4'-piperidine] 
• 59143-11-2 1'-butyryl-3-phenyl-3H-spiro[isobenzofuran-1,4'-piperidine] 
• 59143-21-4 1'-cyclopropylmethyl-3-phenyl-3H-spiro[isobenzofuran-1,4'-piperidine] 

Relevant academic research and scientific papers

Diisobutylaluminum hydride-promoted cyclization of benzyl and phenylsilyl ethers bearing a 2-(trimethylsilyl)ethynyl group: syntheses of indenes and benzosiloles

The reaction of o-[2-(trimethylsilyl)ethynyl]benzyl methyl ethers with diisobutylaluminum hydride (DIBAL-H) gave 2-(trimethylsilyl)indenes in good yields. This cyclization proceeds by regio- and stereoselective hydroalumination of the alkyne moiety followed by intramolecular nucleophilic substitution. o-[2-(Trimethylsilyl)ethynyl]phenylsilyl methyl ethers also underwent the DIBAL-H promoted-cyclization to be converted into 2-(trimethylsilyl)benzosiloles in good yields. This approach provides straightforward and efficient way to construct benzosiloles from readily available organosilanes.

Synthesis of substituted biaryls through gold-catalyzed petasis-ferrier rearrangement of propargyl ethers

Au-catalyzed cycloisomerization of aryl propargyl ethers provides controlled transition from alkyne to carbonyl chemistry followed up by a Petasis-Ferrier rearrangement/aromatization cascade leading to substituted biaryls with functionalized naphthalene cores. An Au-catalyzed sequence of alkoxy group translocation, Petasis-Ferrier rearrangement, and aromatization transforms aryl propargyl ethers into substituted biaryls with functionalized naphthalene cores. Copyright

Synthesis of spiro[isobenzofuran 1(3H),4' piperidines] as potential central nervous system agents

Synthesis of 1' methyl 3 phenylspiro[isobenzofuran 1(3H),4' piperidine] (7a, HP 365) and the demethyl analogue 9a (HP 505) was prompted by recognition of an aminoalkyl(aryl)isobenzofuran moiety common to the antidepressants talopram (Lu 3-010) and trans 10,11 dihydro 5,10 epoxy 5 [3 (methylamino)propyl] 5H dibenzo[a,d]cyclohepten 11 ol (MK-940). Convenient laboratory synthesis of 7a was provided by lithiation of 2 bromobenzhydryl methyl ether, followed by addition of 1 methyl 4 piperidone and acid catalyzed cyclization. N Dealkylation by standard methods afforded 9a. Synthesis of analogues was stimulated by discovery of marked inhibition of tetrabenazine induced ptosis for lead compounds 7a and 9a. Optimal antitetrabenazine activity is associated with the 3 phenylspiro[isobenzofuran 1(3H),4' piperidine] moiety where nitrogen is basic. Modification of this moiety by introduction of large nitrogen substituents or a C-3 substituent > H significantly reduced antitetrabenazine activity. A series of analogue with aromatic substituents was investigated; however, few of these compounds were significantly more active than 7a and 9a. Compound 9a was selected for additional studies.

3-Aminoalkyl-1,3-dihydro-3-phenylspiro[isobenzofurans]

Substituted 3-aminoalkyl-1,3-dihydro-3-phenylspiro[isobenzofurans] possessing tranquilizing properties, and process for the preparation thereof are described.